As disclosed in U.S. Pat. No. 3,480,671, the compound N,N-diethyl-2(.alpha.-naphthoxy)propionamide has been found to be a useful herbicide. As described in that patent, it was prepared by reacting .alpha.-naphthol with N,N-diethyl-.alpha.-bromopropionamide in the presence of a 25% solution of sodium methoxide in methanol. The melting point of the product is given as 63.degree.-64.degree. C. However, preparation by this process produced a product in insufficient yield and with a purity below the minimum acceptable commercial level. It was subsequently proposed to produce this compound through the intermediate 2(.alpha.-naphthoxy) propionic acid, ##STR2## by reacting .alpha.-naphthol with .alpha.-chloropropionic acid. However, the production of this intermediate is somewhat expensive and in addition, the yields of the desired product from .alpha.-naphthol were at about the 50% level. Among the by-products were compounds having a furan-type ring condensed with the naphthalene ring, which are difficultly separable from the desired product.
It is an object of this invention to provide an improved process for the production of N,N-diethyl-2(.alpha.-naphthoxy) propionamide from .alpha.-naphthol.
A further object of this invention is to provide a process for production of N,N-diethyl1-2(.alpha.-naphthoxy)propionamide of good purity and in acceptably high yield from .alpha.-naphthol.
A third object of this invention is to provide a process for production of N,N-diethyl 2(.alpha.-naphthoxy)propionamide from .alpha.-naphthol without requiring the use of sodium methoxide.
Other objects and advantages of this invention will be apparent from the description which follows.